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United Staes
atent “
RC6
3,020,253
Patented Feb. 6, 1962
2
1
The» proportions of the difur-furyl terephthalate em
ployed in combination with the vinyl halide resin may
3,020,253
_
PROCESS OF PLASTICIZING A VINYL CHLORIDE
be varied within wide limits. Generally, I prefer to em
RESIN WITH DITETRAHYDROFURFURYL TER
ploy from 10 to 70 percent of the plasticizer based on
EPHTHALATE AND PRODUCT OBTAINED
the total weight of the vinyl halide resin and the plas
THEREBY
_
ticizer, and preferably within the range of from 25 to
Robert M. Lukes, Lawrence. Park, Pa., assignor to Gen
60 percent of the ditetrahydrofurfuryl terephthalate,
eral Electric Company, a corporation of New York
based on the total weight of the latter and the vinyl
No Drawing. Filed June 26, 1958, Ser. No.,744,649
halide resin.
6 Claims. (Cl. 260-30.4)
.
10
In addition, heat stabilizers, such as lead oxide, lead
silicate, tribasic lead sulfate, lead carbonate, etc., in
This invention relates to plasticized‘vinyl resins- More
amounts ranging from about 0.5 to 10 to 15 percent, by
particularly, the invention is concerned with vinyl halide
weight, based on the weight of. the vinyl halide resin
-resins plasticizedwith a composition comprising ditetra
may be incorporated. In addition, various ?llers, such
hydrofurfuryl terephthalate having the formula
15 as lithopone, titanium dioxide, etc., as well as other
common plasticizers, for instance, dioctyl phthalate, tri
cresyl phosphate, etc., pigments and other modifying
materials may be incorporated without detrimental effects
on the heat, light, and electrical stability of the plasti
One of the difficulties in ?nding a suitable plasticizer 20 cized materials.
for vinyl halide resins is to ?nd one which gives, in part,
su?‘icient ?exibility to the vinyl halide resin as evidenced.
In order that those skilled in the art may better under
stand how the present invention may be practiced, the
following examples are given by way of illustration and
not by way of limitation. All parts are by weight.
in some respects by elongation without adversely atfect-'
ing the tensile strength of the plasticized composition.
Unexpectedly, I have discovered that a speci?c plasticizer, 25
Example 1
namely, ditetrahydrofurfuryl terephthalate (hereinafter
A mixture of 300 grams of tetrahydrofurfuryl alcohol,
166 grams terephthalic acid, and 10 grams of p-toluene»
vinyl halide resin to give a product which has good ten
sulfonic acid (33% aqueous solution) was heated until
sile strength and yet has outstanding percent elongation
and ?exibility. The discovery that the ditetrahydrofur 30 50 ml. water had distilled. The ?nal temperature of
the mixture was 230° C. The mixture was cooled and
furyl terephthalate was able to impart these outstanding
dissolved in 600 ml. chloroform and this solution was
properties simultaneously to the vinyl halide resin when
referred to as “difurfuryl ester”) is able to plasticize a
washed with 500 ml. water. and then with 1000 ml. of
2 M aqueous potassium bicarbonate solution. The chlo
ployed, for instance, a very similar compound, namely, 35 roform solution was dried over anhydrous sodium sul
fate, ?ltered and evaporated on a steam bath. The resi
iditetrahydrofurfuryl o-phthalate, it was found that both
due was distilled under vacuum and 400 grams of ditetra
the tensile strength and the percentage elongation were
hydrofurfuryl terephthalate boiling at ZOO-203° C. (0.3
substantially lower than was obtained by using my above
mm.) and having a melting point of 55~S6° C. was ob
described difurfuryl ester.
The vinyl halide resins capable of being plasticized 40 tained. Analysis of this compound showed it to be the
desired terephthalate as evidenced by the fact that it
by the difurfuryl ester may be such compositions as,
contained 64.19% carbon and 7.0% hydrogen as con
for example, (1) the polyvinyl halides, such as, for in
trasted to theoretical amounts of 64.65% carbon and
stance, polyvinyl chloride (including the diiierent molec
employed as a plasticizer was entirely unexpected and in
no way could have been predicted since when one em
6.63% hydrogen.
ular weight forms, e.g., gamma polyvinyl chloride, etc.),
polyvinyl bromide, etc.; (2) vinyl resins produced by the 45
conjoint polymerization of a vinyl halide, for example,
vinyl chloride and a vinyl ester of a lower saturated ali
phatic monocarboxylic acid, for instance, vinyl acetate
(such vinyl chloride-vinyl acetate copolymers being
Example 2
In order to compare the advantages of this terephtha
late ester with another similar. ester, particularly ditetra
hydrofurfuryl o-phthalate, the latter ortho phthalate was
prepared in accordance with the directions described in '
available under the trade name of “Vinylite” resin where-, 50 Japanese Patent 3,686 (1951). ,
in the vinyl chloride component is present in a prepon
derant amount), vinyl propionate, vinyl butyrate, vinyl
hexoate, vinyl acetobutyrate, vinyl chloroacetate, vvinyl
Example 3
Each of the plasticizers described in Examples 1 and 2
chloroprionate, etc., it being understood from the fore
was mixed with gamma polyvinyl chloride in an amount
going examples that the term “lower saturated aliphatic 55 equal to 60 parts of the polyvinyl chloride and 40 parts
monocarboxylic acid” embraces ones containing at most
six carbon atoms; (3) vinyl resins produced by the con
joint polymerization of a vinyl halide and an acrylic
compound; .(4) ’ copolymers of vinyl halides, for example,
of the terephthalate or ortho-phthalate ester as the case
may be. The two mixtures were molded into the form
of ?at sheets suitable for testing. The sheets were tested
for tensile strength and percent elongation with the fol
vinyl chloride, and a vinylidene halide (e.g., vinylidene 60 lowing results. The polyvinyl chloride plasticized with
chloride), etc.; and (5) many other vinyl resin copoly
the ditetrahydrofurfuryl ortho-phthalate had a tensile of
mers, such as the copolymers of three component sys—
tems, for instance, vinyl chloride, vinyl acetate, and ethyl
about 2923 p.s.i. and a percent elongation of about
> 234%. In contrast to this, the polyvinyl chloride plas
methacrylate. As will be understood by those skilled in
ticizedwith the ditetrahydrofurfuryl terephthalate had a
the art, other multi-component copolymers may be used, 65 tensile strength of 3260 p.s.i. and a percent elongation
the only requirement being that at least one of the com
of 400%.
ponents is a vinyl halide. Further methods of prepara
‘ It will, of course, by apparent to. those skilled in the
tion of vinyl halide resins employed herein and addi~ .7 art_that other vinyl halide resins and other proportions
tional examples of vinyl copolymers which can be plas
of ingredients may be employed without departing from
ticized with the aforementioned ditetrahydrofurfuryl ter 70 the scope of the invention. The claimed plasticized com
ephthalate may be found in D’Alelio Patents 2,378,753
positions can be used for making shower curtains, table
and 2,299,740.
.
cloths, rain coats, etc. They are eminently suitable for V
3,020,268
.
4
i
5. The process for plasticizing a polyvinyl chloride
insulating electrical conductors, particularly copper con
resin which comprises incorporating therein ditetrahydro
ductors.
What I claim as new and desire to secure by Letters
furfuryl terephthalate in an amount wherein the tereph
thalate ester comprises, by weight, from 10 to 70% of
the total Weight of the latter and the polyvinyl chloride.
Patent of the United‘ States vis:
l. A composition of matter composed of a vinyl chlo
ride resin and a plasticizer therefor comprising ditetra
6. The process for plasticizing a vinyl chloride-vinyl
acetate copolymer which comprises incorporating therein
hydrofurfuryl terephthalate.
ditetrahydrofurfuryl terephthalate ester in an amount
2. A composition of matter comprising polyvinyl chlo
wherein the terephthalate comprises, by weight, from 10
to 70% of the total Weight of the latter and the copoly
3. A composition of matter comprising (1) a vinyl 10 ‘mer of vinyl chloride and vinyl acetate.
chloride resin composed of a copolymer of vinyl chlo
ride and vinyl acetate, and (2) a plasticizer therefor
References Cited in the ?le of this’ patent
ride plasticized with ditetrahydrofurfuryl terephthalate.
comprising ditetrahydrofurfuryl terephthalate.
4. The process for plasticizing a vinyl chloride resin
which comprises incorporating therein ditetrahydrofur
furyl terephthalate in an amount wherein the terephtha
late ester comprises, by weight, from 10 to 70% of the
total weight of the latter and the vinyl chloride resin.
UNITED STATES PATENTS
15
2,213,752
Swan ____________ __'__'_ Sept. 3, 1940
R 2,234,615
Alexander __________ __ Mar. 11, 1941
2,259,141v
2,757,180
Russell _____________ __ Oct. 14, 1941v
Dazzi ______________ _.. July 31, 1956
g